Spirotryprostatin A

Spirotryprostatin A is an indolic alkaloid from the 2,5-Diketopiperazine class of natural products found in the Aspergillus fumigatus fungus. Spirotryprostatin A and several other indolic alkaloids (including Spirotryprostatin B, as well as other tryprostatins and cyclotryprostatins) have been found to have anti-mitotic properties, and as such they have become of great interest as anti-cancer drugs.[1] Because of this, the total syntheses of these compounds is a major pursuit of organic chemists, and a number of different syntheses have been published in the chemical literature.

Spirotryprostatin A
Spirotryptostatin A
Names
Preferred IUPAC name
(2S,3S,5aS,10aS)-2′-Hydroxy-6′-methoxy-3-(2-methylprop-1-en-1-yl)-1,5a,6,7,8,10,10a-hexahydro-3H,5H,10H-spiro[dipyrrolo[1,2-a:1′,2′-d]pyrazine-2,3′-indole]-5,10-dione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C22H25N3O4/c1-12(2)9-18-22(14-7-6-13(29-3)10-15(14)23-21(22)28)11-17-19(26)24-8-4-5-16(24)20(27)25(17)18/h6-7,9-10,16-18H,4-5,8,11H2,1-3H3,(H,23,28)/t16-,17-,18-,22-/m0/s1 ☒N
    Key: MQJKGSIAJNXSCM-ORGXJRBJSA-N ☒N
  • CC(=C[C@H]1[C@]2(C[C@@H]3N1C(=O)[C@@H]4CCCN4C3=O)C5=C(C=C(C=C5)OC)NC2=O)C
Properties
C22H25N3O4
Molar mass 395.43 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

One such total synthesis was published in 1999, which showed that the isopropylidene side chain was not necessary to the biological activity of the compound, leading to a number of new theorized analogues.[2]

References
  1. Borthwick AD (2012). "2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products". Chemical Reviews. 112 (7): 3641–3716. doi:10.1021/cr200398y. PMID 22575049.
  2. Edmondson, S; et al. (1999). "Total Synthesis of Spirotryprostatin A, Leading to the Discovery of Some Biologically Promising Analogues". J. Am. Chem. Soc. 121 (10): 2147–2155. doi:10.1021/ja983788i.
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